EP1013653A2 - Ein Organosiliciumendgruppe formende Verbindung mit ein am Silicium-gebundenes Wasserstofatom - Google Patents

Ein Organosiliciumendgruppe formende Verbindung mit ein am Silicium-gebundenes Wasserstofatom Download PDF

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Publication number
EP1013653A2
EP1013653A2 EP99310232A EP99310232A EP1013653A2 EP 1013653 A2 EP1013653 A2 EP 1013653A2 EP 99310232 A EP99310232 A EP 99310232A EP 99310232 A EP99310232 A EP 99310232A EP 1013653 A2 EP1013653 A2 EP 1013653A2
Authority
EP
European Patent Office
Prior art keywords
independently selected
carbon atoms
organosilicon compound
aliphatic unsaturation
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99310232A
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English (en)
French (fr)
Other versions
EP1013653A3 (de
Inventor
Timothy B. Lueder
Richard Alan Palmer
Nick Evan Shephard
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Silicones Corp
Original Assignee
Dow Corning Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dow Corning Corp filed Critical Dow Corning Corp
Publication of EP1013653A2 publication Critical patent/EP1013653A2/de
Publication of EP1013653A3 publication Critical patent/EP1013653A3/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/12—Organo silicon halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Definitions

  • This invention relates to an organosilicon compound comprising one silicon-bonded hydrogen atom.
  • compositions which cure to elastomeric materials at room temperature are well known.
  • Such compositions can be obtained by mixing polydiorganosiloxanes having reactive or hydrolyzable groups, such as silanol or alkoxy groups, with silane crosslinking agents, for example, alkoxysilanes, acetoxysilanes, oximosilanes, aminosilanes and catalysts as needed.
  • silane crosslinking agents for example, alkoxysilanes, acetoxysilanes, oximosilanes, aminosilanes and catalysts as needed.
  • the polydiorganosiloxanes have 1 to 3 reactive groups per chain end. Compositions comprising these ingredients can then be cured by exposure to atmospheric moisture at room temperature.
  • the cure rate of a particular composition is dependent on a number of factors including the type of reactive or hydrolyzable group utilized. It is known that different hydrolyzable groups have different reactivities and even the same type of hydrolyzable group can have different reactivities. For example, in the presence of moisture, a silicon-bonded acetoxy group will hydrolyze more rapidly than a silicon-bonded alkoxy group.
  • each silicon-bonded alkoxy group has a different reactivity, with the alkoxy group first reacted being "most reactive.”
  • the first alkoxy group on a silicon atom reacts it takes a longer time for the second alkoxy group on the same silicon atom to react, and even longer for the third. Therefore, it would be desirable to prepare an organosilicon compound which can endcap a polymer and be capable of providing more than one "most" reactive hydrolyzable group per polymer chain end.
  • An objective of the present invention is to prepare an organosilicon compound comprising one silicon-bonded hydrogen atom which is capable of endcapping a polymer and providing more than one "most" reactive hydrolyzable group per polymer chain end.
  • the present invention is an organosilicon compound comprising one silicon-bonded hydrogen atom described by formula or by formula where each R 1 and R 1' is an independently selected hydrocarbon radical free from aliphatic unsaturation having 1 to 18 carbon atoms; each R 2 is an independently selected hydrocarbon radical free from aliphatic unsaturation having 1 to 18 carbon atoms; each X and X' is independently selected from halogen, alkoxy, acyloxy or ketoximo; t is 2 or 3; n is 0, 1 or 2; and each Z is independently selected from divalent hydrocarbon radicals free of aliphatic unsaturation having 2 to 18 carbon atoms and a combination of divalent hydrocarbon radicals and siloxane segments.
  • the present invention is an organosilicon compound comprising one silicon-bonded hydrogen atom described by formula or by formula where each R 1 and R 1' is an independently selected hydrocarbon radical free from aliphatic unsaturation having 1 to 18 carbon atoms; each R 2 is an independently selected hydrocarbon radical free from aliphatic unsaturation having 1 to 18 carbon atoms; each X and X' is independently selected from halogen, alkoxy, acyloxy and ketoximo; t is 2 or 3; n is 0, 1 or 2; and each Z is independently selected from divalent hydrocarbon radicals free of aliphatic unsaturation having 2 to 18 carbon atoms or a combination of divalent hydrocarbon radicals and siloxane segments described by formula where R 2 is as defined above; each G is an independently selected divalent hydrocarbon radical free of aliphatic unsaturation having 2 to 18 carbon atoms; and c is a whole number from 1 to 6.
  • each R 1 is an independently selected hydrocarbon radical free from aliphatic unsaturation having 1 to 18 carbon atoms.
  • the hydrocarbon radicals free from aliphatic unsaturation represented by R 1 may be substituted or unsubstituted.
  • hydrocarbon radicals free from aliphatic unsaturation include alkyl radicals, aryl radicals and aralkyl radicals.
  • alkyl radicals include methyl, ethyl, hexyl, octadecyl, cyclobutyl, cyclopentyl, cyclohexyl, 3,3,3-trifluoropropyl, chloromethyl and chlorocyclopentyl.
  • each R 1 is selected from alkyl radicals having 1 to 8 carbon atoms and aryl radicals having 6 to 8 carbon atoms. More preferably, R 1 is an alkyl radical having 1 to 8 carbon atoms. Most preferably, R 1 is n-propyl.
  • each R 1' is an independently selected hydrocarbon radical free from aliphatic unsaturation having 1 to 18 carbon atoms.
  • the hydrocarbon radicals free from aliphatic unsaturation represented by R 1' may be substituted or unsubstituted.
  • Examples of hydrocarbon radicals free from aliphatic unsaturation include alkyl radicals, aryl radicals and aralkyl radicals. Examples of R 1' are as described above for R 1 .
  • each R 1' is selected from alkyl radicals having 1 to 8 carbon atoms and aryl radicals having 6 to 8 carbon atoms. More preferably, R 1' is an alkyl radical having 1 to 8 carbon atoms. Most preferably, R 1' is methyl.
  • each R 2 is an independently selected hydrocarbon radical free from aliphatic unsaturation having 1 to 18 carbon atoms.
  • the hydrocarbon radicals free from aliphatic unsaturation represented by R 2 may be substituted or unsubstituted.
  • Examples of hydrocarbon radicals free from aliphatic unsaturation include alkyl radicals, aryl radicals and aralkyl radicals. Examples of R 2 are as described above for R 1 .
  • each R 2 is an independently selected alkyl radical. More preferably each R 2 is an independently selected alkyl radical having 1 to 8 carbon atoms. Most preferably each R 2 is methyl.
  • each X is independently selected from the group consisting of halogen, alkoxy, acyloxy and ketoximo.
  • the halogen atoms can be chlorine, bromine, fluorine and iodine.
  • alkoxy groups include methoxy, ethoxy, iso-propoxy, butoxy, cyclohexoxy, phenoxy, 2-chloroethoxy, 3,3,3-trifluoropropoxy, 2-methoxyethoxy and p-methoxyphenoxy.
  • alkoxy groups include methoxy, ethoxy, iso-propoxy, butoxy, cyclohexoxy, phenoxy, 2-chloroethoxy, 3,3,3-trifluoropropoxy, 2-methoxyethoxy and p-methoxyphenoxy.
  • acyloxy groups include acetoxy, propionoxy, benzoyloxy and cyclohexoyloxy.
  • ketoximo groups include dimethylketoximo, methylethylketoximo, methylpropylketoximo, methylbutylketoximo and diethylketoximo.
  • each X is independently selected from alkoxy, acyloxy and ketoximo. More preferably each X is independently selected from alkoxy and acyloxy, with each X being an independently selected alkoxy group being most preferred.
  • each X' is independently selected from the group consisting of halogen, alkoxy, acyloxy and ketoximo. Examples of X' are as described above for X. Preferably each X' is independently selected from alkoxy, acyloxy and ketoximo. More preferably, each X' is independently selected from alkoxy and acyloxy, with each X' being an independently selected alkoxy group being most preferred.
  • subscript t is 2 or 3 and is preferably 2.
  • n is 0, 1 or 2 and is preferably 0 or 1.
  • each Z is independently selected from divalent hydrocarbon radicals free of aliphatic unsaturation having 2 to 18 carbon atoms or a combination of divalent hydrocarbon radicals and siloxane segments described by formula where R 2 is as defined above; each G is an independently selected divalent hydrocarbon radical free of aliphatic unsaturation having 2 to 18 carbon atoms; and c is a whole number from 1 to 6.
  • Examples of the divalent hydrocarbon radicals free of aliphatic unsaturation represented by Z and G include alkylene radicals, arylene radicals and aralkylene radicals.
  • the divalent hydrocarbon radicals represented by Z and G may be substituted or unsubstituted.
  • alkylene radicals include ethylene, methylmethylene, propylene, butylene, pentylene, hexylene, cyclopentylene, cyclohexylene, chloroethylene and chlorocyclopentylene.
  • Examples of arylene radicals include phenylene, tolylene, xylylene, 2,4-dichlorophenylene and tetrachlorophenylene.
  • aralkylene radicals examples include benzylene, beta-phenylethylene, gamma-tolylpropylene, para-chlorobenzylene and 2(bromophenyl)propylene.
  • Z is a combination of divalent hydrocarbon radicals and siloxane segments as described above, each G is preferably an independently selected alkylene radical, and each G is more preferably an independently selected alkylene radical having 2 to 8 carbon atoms.
  • each Z is an independently selected divalent hydrocarbon radical free from aliphatic unsaturation. It is more preferred for each Z to be an independently selected alkylene radical, with an independently selected alkylene radical having 2 to 8 carbon atoms being most preferred for each Z.
  • the organosilicon compound comprising one silicon-bonded hydrogen atom described by formula (I) may be prepared by mixing an organohydrogensiloxane described by formula R 1 4-(t+1) Si-(O-SiR 2 2 H) t+1 (II) with an organosilicon compound containing one aliphatic unsaturation described by formula Y-SiR 2 n X 3-n (III).
  • the organosilicon compound comprising one silicon-bonded hydrogen atom described by formula (IA) may be prepared in a similar manner by mixing an organohydrogensiloxane described by formula with an organosilicon compound containing one aliphatic unsaturation described by formula Y-SiR 2 n X' 3-n (IIIA), in each case in the presence of a hydrosilylation catalyst, where R 1 , R 1' , R 2 , X, X', t and n are as defined above and Y is selected from hydrocarbon radicals comprising one aliphatic unsaturation and 2 to 18 carbon atoms and a combination comprising one aliphatic unsaturation of hydrocarbon radicals, siloxane segments and a divalent hydrocarbon radical free of aliphatic unsaturation having 2 to 18 carbon atoms described by formula where R 2 , G and c are as defined above and M is an independently selected hydrocarbon radical comprising one aliphatic unsaturation and 2 to 18 carbon atoms.
  • the hydrocarbon radicals represented by Y and M may be substituted or unsubstituted.
  • Examples of the hydrocarbon radicals comprising one aliphatic unsaturation represented by Y and M include alkenyl radicals such as vinyl, allyl, butenyl, hexenyl, octenyl and cycloalkenyl radicals such as cyclopentenyl, cyclohexenyl and chlorocyclopentenyl.
  • alkenyl radicals such as vinyl, allyl, butenyl, hexenyl, octenyl and cycloalkenyl radicals such as cyclopentenyl, cyclohexenyl and chlorocyclopentenyl.
  • G be an alkylene radical and M an alkenyl radical, and more preferable that G be an alkylene radical having 2 to 8 carbon atoms and M an alkenyl radical having 2 to 8 carbon atoms.
  • Y is a hydrocarbon radical comprising one aliphatic unsaturation. It is more preferred for Y to be an alkenyl radical, with an alkenyl radical having 2 to 8 carbon atoms being most preferred for Y.
  • the organohydrogensiloxanes described by formula (II) may be prepared by known methods such as taught in U.S. Patent 5,446,185.
  • the organohydrogensiloxanes described by formula (IIA) may also be prepared by known methods.
  • the organosilicon compounds containing one aliphatic unsaturation described by formulas (III) and (IIIA) may also be prepared by known methods and are commercially available.
  • Catalysts typically employed for hydrosilylation reactions such as platinum group metal-containing catalysts are used as catalysts for the reaction between the organohydrogensiloxane described by formula (II) or (IIA) and the organosilicon compound containing one aliphatic unsaturation described by formula (III) or (IIIA), respectively .
  • platinum group metal it is meant ruthenium, rhodium, palladium, osmium, iridium and platinum.
  • Platinum group metal-containing catalysts particularly useful in the present composition are the platinum complexes prepared as described by U.S. Patents 3,419,593 and 5,175,325.
  • Preferred catalysts are complexes of. platinum with vinylsiloxane.
  • the amount of catalyst useful in effecting the hydrosilylation reaction to make the composition of the present invention is not narrowly limited as long as there is an amount present for accelerating a reaction between the hydrosilyl groups and the groups comprising an aliphatic unsaturation.
  • the appropriate amount of the catalyst will depend upon the particular catalyst used. In general as low as 0.1 part by weight of platinum group metal based on 1 million parts by weight of total reactants may be useful (ie. 0.1 ppm).
  • the amount of platinum group metal is from 1 to 60 ppm. More preferred is from 10 to 40 ppm platinum group metal.
  • the platinum group metal-containing catalyst may be added as a single species or as a mixture of two or more different species. Adding the catalyst as a single species is preferred.
  • the temperature of the hydrosilylation reaction is not strictly specified, but usually falls within the range of 20° to 150°C. and preferably within the range of 30° to 110°C.
  • the molar ratio of aliphatic unsaturated groups to hydrosilyl groups useful in the present invention will vary depending upon the individual compositions. However, to ensure the highest yield of the organosilicon compound comprising one silicon-bonded hydrogen atom, the molar ratio of aliphatic unsaturated groups to hydrosilyl groups should be t/t+1:1, where t is as defined above.
  • the organosilicon compound comprising one silicon-bonded hydrogen atom described by formulas (I) and (IA) may be recovered by standard methods for separating liquid mixtures, such as by distillation from the reaction mixture under reduced pressure, recrystallization or solvent fractionation.
  • the distilled reaction mixture containing the organosilicon compound comprising one silicon-bonded hydrogen atom described by formula (IA) may also contain isomers of this compound depending on which specific hydrogen atoms react.
  • More preferred compounds of the invention are and where Propyl is n-propyl and Me is methyl , with the latter compound being most preferred.
  • the method of preparing the latter compound is also preferred because a larger, improved yield of the adduct containing one silicon-bonded hydrogen atom is obtained.
  • organosilicon compounds comprising one silicon-bonded hydrogen atom of the present invention are useful for endcapping polymers and as adhesion promoters and crosslinkers.
  • Polymers endcapped with the organosilicon compounds of the present invention can be used for preparing sealants, adhesives and coatings.
  • the organosilicon compounds of the present invention in addition to endcapping polymers may also be found pendant on the polymer chain.
  • Me is methyl and Propyl is n-propyl.
  • the gas liquid chromatograph used to analyze each composition was a Hewlett Packard 5890 Series II with a flame ionization detector.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Silicon Polymers (AREA)
EP99310232A 1998-12-21 1999-12-20 Ein Organosiliciumendgruppe formende Verbindung mit ein am Silicium-gebundenes Wasserstofatom Withdrawn EP1013653A3 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US21853498A 1998-12-21 1998-12-21
US09/456,424 US6265518B1 (en) 1998-12-21 1999-12-08 Organosilicon endcapper having one silicon-bonded hydrogen atom
US456424 1999-12-08
US218534 1999-12-08

Publications (2)

Publication Number Publication Date
EP1013653A2 true EP1013653A2 (de) 2000-06-28
EP1013653A3 EP1013653A3 (de) 2001-09-26

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EP99310232A Withdrawn EP1013653A3 (de) 1998-12-21 1999-12-20 Ein Organosiliciumendgruppe formende Verbindung mit ein am Silicium-gebundenes Wasserstofatom

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US (1) US6265518B1 (de)
EP (1) EP1013653A3 (de)
JP (1) JP2000212190A (de)
KR (1) KR20000052531A (de)

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